Here I think is the point, that one may disagree with what Bain Capital did, but it’s difficult to say that, in performing that job, Romney was bad at it. Attacking Bain Capital does at least as much harm to Obama’s campaign as it does good. You may be able to sell the message that what he did helped lead to fewer jobs and damaging the economy, but you can’t really sell that message without also telling us that Romney has an understanding of the economy and was a competent business man. If the economy is going to be a major issue, that you’d have to straight up concede that he’s well qualified on matters of business and economics would kill, especially since there’s at least some reasoning that, even if what he was doing was destroying jobs, he did that job effectively, and now trying to create jobs, being so knowledgeable about the economy and business, he would be effective at that too.
Worse than that, even if he does manage to sell the moral aspects of that argument to his advantage, it carries additional baggage. Obviously, it will piss off some other financial people which could mean either less contributions for him or more for Romney. It will also continue to emphasize to the public how corrupt the financial system is, sure if he sells it, Romney is a part of it, but Obama still is reducing confidence in the economy and financial situation of the country.
I think it’s only a winning move for Obama if Romney just can’t successfully defend himself at all; however, I think Romney has enough talking points to at least minimize the damage the attacks can do to him, so short of handling it with utter incompetence, I think it’s a net loss for Obama. He’ll do much better emphasizing his own accomplishments as president in improving the economy than pressing that issue.